


Casually Together

by SummerRoses0612



Series: Prompts/Pairings [8]
Category: Teen Wolf (TV)
Genre: Alpha Derek Hale, Anal, Anal Fingering, Anal Sex, Aromantic, Aromantic Derek Hale, Aromantic Stiles Stilinski, Bisexual Stiles Stilinski, Bisexual Vernon Boyd, Bottom Aiden (Teen Wolf), Bottom Derek Hale, Bottom Vernon Boyd, Confident Stiles Stilinski, Consensual Underage Sex, DO NOT COPY, Frottage, Gay Aiden, Gay Derek Hale, Gay Sex, M/M, Magical Stiles Stilinski, Oral Sex, Past Underage, Plot What Plot/Porn Without Plot, Porn, Research, Researcher Stiles Stilinski, Rimming, Romance Repulsed Stiles Stilinski, Rough Oral Sex, Rough Sex, Rutting, Self-Discovery, Sex, Shower Sex, Spark Stiles Stilinski, Stiles Stilinski Gives Oral Sex, Stiles Stilinski Has Sex, Stiles Stilinski Has a Big Dick, Stiles Stilinski Wants Sex, Stiles Stilinski is Not a Virgin, Stiles Stilinski is a Cock Tease, Stiles Stilinski is a Little Shit, Stiles Stilinski is a Tease, Stiles Stilinski is a slut, Summer Romance, Top Stiles Stilinski, Underage Kissing, Underage Sex, Versatile Stiles Stilinski, Versatile Vernon Boyd, Werewolf Aiden, Werewolf Derek Hale, Werewolf Vernon Boyd, do not copy to another site, romance repulsed
Language: English
Status: Completed
Published: 2021-01-03
Updated: 2021-01-05
Packaged: 2021-03-12 20:49:09
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 3
Words: 3,856
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28516683
Author URL: https://archiveofourown.org/users/SummerRoses0612/pseuds/SummerRoses0612
Summary: Stiles likes to have sex, not that anyone that really knows him is surprised. These are his adventures with casual sex and the supernatural mixing.
Relationships: Aiden/Stiles Stilinski, Derek Hale/Stiles Stilinski, Stiles Stilinski/Original Female Character(s), Vernon Boyd/Stiles Stilinski
Series: Prompts/Pairings [8]
Series URL: https://archiveofourown.org/series/2182707
Comments: 4
Kudos: 90





	1. Boyd

**Author's Note:**

> DISCLAIMER: I don't own Teen Wolf or anything else.
> 
> Warning- This story contains: Sex. Lots of it. 
> 
> Read the tags blah blah blah. Off of another two prompts from notyourtipicalauthor, hope you like it!

Stiles had had sex for the first time when he was sixteen. The girl was pretty, experienced, and perfectly nice, miles of tan skin and dark eyes. It was a summer fling but, when it ended, the teen realized that he was never really that into it. The sex was great, the conversation was amazing but the romantic stuff that she had tried to do with him made his skin crawl. Stiles was confused at first, every single guy that he knew would have been happy to have a relationship with someone like her but, instead of understanding the envy that others would feel all he could wonder was why people would want a relationship anyways. 

He mentioned it to Scott, expecting that the other teen would feel the same way, only to get a weird look and increasingly concerned questions. Someone up above must have been listening because Scott never mentioned it his mom and thus his dad never knew, crisis averted. Right?

Wrong

His next relationship went much the same way. Amazing girl that he was more than happy to be with, sex and movies and conversations. Then she said that she was getting real feelings for Stiles. 

His skin instantly started crawling

He let her down easy, platitudes of 'I'm not looking for a relationship right now' and 'It's not you it's me' coming much easier than he ever expected the words to. They parted on good terms, neither having really been invested quite yet, and occasionally had sex when they were looking for a booty call. 

More research later and two terms jumped out at him like water in a desert.

_Aromantic_

_Romance Repulsed_

Everything dating was easier after that, casual sex and lots of cuddling with Scott later and he felt better than he had since he had sex the first time. When someone hit on him it still made him want to heave but, what made all the difference, was that he wasn't confused as to why. 

Which was why he didn't actually realize that Boyd was flirting with him until the tell tale goosebumps and revulsion started.

He left it alone for one week, let himself make sure that the wolf was really flirting with him, before he cornered Boyd to talk to him. 

The school was quiet, the last bell having rung about thirty minutes ago and everyone hauling ass to get away from the cursed building. He found the wolf he needed to talk to in the locker rooms, the teen was showing so Stiles made sure to be loud enough that Boyd couldn't miss it. 

"Do you have a minute to talk?" Stiles asked once he was sure that the werewolf wouldn't be surprised by his voice.

"Sure, what's up?" Boyd was still silent most of the time, but when he was relaxed and around the pack he was a little more talkative. His voice was deep and sent shivers down Stiles' spine, only making him more aware that he might make the other teen uncomfortable but pushing past it anyways. 

"I'm pretty sure that you've been flirting with me, I'm sorry in advance if I was wrong, and I just wanted to tell you that I'm aro. It means that I'm not into romantic relationships." 

Stiles let out a breath of relief when Boyd didn't look confused, just thoughtful.

"I was trying to get into your pants, not necessarily date you. Does that mean you won't have sex with me?" 

The teens made eye contact for a second before laughing, leaning against each other at how stupid the situation was. Then they were kissing, teeth and tongue battling before the werewolf let Stiles win.

Stiles was taller by a couple inches but lithe and lightly toned where Boyd was all hard muscle and quarterback build. Their kisses didn't have any of the sappy edge that made the romance repulsed teen want to run, letting him dominate the lip lock and just enjoy it. 

Boyd was already naked from his shower and Stiles quickly followed, taking his layers of shirts as quickly as he could before backing the werewolf into the cold tile wall. The wolf hissed at the cold but just laughed with the Spark at sound he had made. The shower was still on, the water slicking their bodies to allow them to rut against each other. They grinded against each other for a little while, panting noises swallowed by the ferocity of their kisses, before it just wasn't enough. 

Boyd pulled away for a moment and grabbed a packet of lube from his backpack, getting another laugh out of the other teen. They went back to rubbing against each other as Stiles took the lube.

"Top or bottom?" Stiles was panting around the words, his hands everywhere he could get them but avoiding the dark cock rubbing into his stomach. 

"Bottom."

With his answer the pale teen ripped open the lube and oiled his fingers and cock, using the excess to jerk the dark skinned teen off while he fingered him. Stiles quickly realized that Boyd like it a little rough, his keening moans giving him away when the brown haired teen shoved a single finger past the protective muscles with no finesse. The Spark just chuckled, instantly adding another finger to the wolf's hole and kissing him. 

The prep went quickly after that, two fingers turning into three then four when Stiles just couldn't resist.

"I'm ready!" Boyd practically hissed to Stiles, getting a huff of choked laughter.

The Spark took the fingers away roughly and pounded right into the werewolf's hole with no mercy, practically holding Boyd up against the wall of the shower when the teen's knees went weak. Boyd practically wailed as he was filled, his hands turning into claws and digging into Stiles' back. The other teen just groaned in ecstasy at the feeling of Boyd's tight, wet walls around him and the edge of pain brought from the claws in his back.

He check on the werewolf quickly, taking in the intense pleasure and desperate rutting before he pulled out almost all the way slowly. He made the werewolf feel every inch, bump, and vein as he withdrew before pushing back in roughly and hit Boyd's prostate head on. He went on like this for what felt like hours, slow withdraw rough, brutal, pounding in strokes that hit the wolf's pleasure spot every time.

It didn't take Boyd long before he was moaning in time with the vicious thrusts, every line in his body begging for release from the clench of his stomach and how much harder he was clawing up Stiles' back. His eyes were flashing, the overwhelming pleasure not allowing him a second or catch his breath or control himself. 

Stiles, finally on the edge of coming, reached between them and painstakingly slowly stroked Boyd until the other teen finally came. Boyd's entire body tightened, his vise like grip on Stiles' cock bringing the Spark over with him. 

When they finally came back to themselves they were sitting on the floor, Stiles panting into the werewolf's neck and straddling him. The pale teen pulled his cock out of the dark skinned boy and helped him up. 

They showered, cleaning each other up, before they walked to the parking lot. 

"I had fun, I'd love to do it again if you're looking for a booty call." Stiles said, kissing Boyd one more time before going to his car.

Boyd just nodded and walked to the other side of the lot. 

They were definitely going to do that again.

* * *

_I suddenly realized that I've been writing a lot of porn lately. Anyways, hope you enjoyed! Comments are always welcome. -Rose_


	2. Aiden

Getting pulled into empty classrooms by werewolves hasn't been weird to Stiles for a long time now. So, when a strong arm reached out and grabbed him he didn't struggle, knowing it probably wouldn't do any good anyways. 

Aiden was the face that met his, his beautiful blue eyes and light brown hair standing out in the dark room. He was taller than stiles by half an inch but had a much stronger build and tan skin, his jaw sharp with 5 o'clock stubble. They had been each other's booty call when they wanted something more rough since the summer before Stiles knew who the Alpha really was. He found out after the second time they had sex and, upon hearing the story and meeting Ethan he felt absolutely no guilt at continuing to fuck around with the wolf. They got right down to business, kissing with teeth and tongues getting in the way just how they liked it. Stiles asked a silent question that he immediately got to work on when the wolf just nodded. 

Stiles pulled both their pants down, biting hickeys into Aiden's neck as he gracefully fell to his knees. The Alpha's cock was girthy and veiny, the head already leaking and red with want. The pale human instantly started to jack him off, getting a feel for the flesh in his hand before starting. He gave kitten licks to get Aiden's cock wet, teasing the slit with his tongue and pushing on the glands with two fingers. Stiles gently swallowed the werewolf's cock, making sure not to choke himself and just doing it slowly like that for a couple minutes. 

Aiden's noises were getting increasingly desperate at the snail's pace, his clawed hands pushing lightly on the back of Stiles' head. The human just continued until he was finally ready before nodding, the wolf instantly thrusting roughly all the way into the back of Stiles' throat. The human did nothing except swallow hard, taking the rough treatment with a hum of pleasure as he let his hands wander. 

He focussed on keeping his jaw relaxed while he touched everywhere he could reached, thoroughly enjoying the growls and grunts of pleasure from the teen in front of him. Stiles gently rolled Aiden's balls, the soft touch contrasting heavily with the rough pace of the wolf's thrusting and only making the other teen all the more desperate. Moving further back the human found the wolf's hole already lubed and stretched. He moaned in surprise and pleasure and moaned again when the cock in his mouth moved harder at the vibrations. Stiles shoved three fingers inside Aiden with no mercy, his rim opening under the pressure with only a little coaxing. 

Stiles had been sucking Aiden's cock long enough that his jaw ached and his throat burned, yet loved every minute. The fingers Stiles had inside the wolf instantly went for the prostate and that was it. 

Aiden's entire body spasmed under the pleasure as he shot his seed down the human's throat, holding Stiles down so that his nose was touching the wolf's stomach. By the time he finally had the weir withdraw to let Stiles up to breathe the human was almost desperate to come. Not giving Aiden any time to recover, his entire body still shaking, he pulled out his fingers and manhandled the werewolf into bending over a spare desk. 

The human immediately spread Aiden's cheeks just to watch him squirm. When the wolf was finally right on the edge of begging and his healing had kicked in enough that he would feel everything Stiles pounded into him. Groaning at the heat but never letting up his hammering thrusts. 

He brought one of his hands off Aiden's hip to cover his mouth, his high pitched noises beautiful but bound to get them caught. Stiles was thrusting as hard as he could, experience with Aiden telling him that the wolf could take it and allowing him to aim right for the prostate. 

Aiden never stopped making noise; high pitched, desperate, and overwhelmed in every line of his body as he begged for more. The human didn't let up until he was about ready to come, pinching the wolf's nipples to make him come for the second time. 

The wolf orgasmed hard, his full body trembling and flinching every time Stiles thrust into him but never asking to stop. Stiles was only able to get a couple more thrusts into the vise like grip Aiden had on his cock before he came too, resting over the Alpha's back and gently rubbing his sides. 

They were both sweating buckets, that saying more for Stiles' stamina than Aiden's, and exhausted. The human gently pulled out, soothing Aiden with a hand on his back when the wolf whined at the empty feeling. Stiles just grabbed his under shirt and carefully wiped them both down, holding Aiden still with a hand on his hip when the wolf whimpered as the human tenderly got his own come out of the Alpha's puffy, tired hole. 

Stiles dressed Aiden and himself, the both of them just resting on the floor and passing a water bottle back and forth until they felt like they could use their legs again properly. 

Aiden kissed Stiles before gingerly moving to get up, giving the human a grateful smile when Stiles got up and helped him. They stayed a while longer, Aiden moaning under the massage that the human was giving his lower back from the rough treatment. 

They both walked out to the cafeteria, the pack somehow blind to the smell of sex on Stiles and Ethan teasing his twin ruthlessly. 

_'Definitely worth it'_ Stiles thought as he watched Aiden wince as he sat down, still limping slightly by the time lunch was done an hour later. 

* * *

_Let me know what you think? Prompts/pairings you'd like to see from me are welcome, as always. -Rose_


	3. Derek

Stiles had never actually seen violence used as foreplay in anything other than shitty romance movies until he met Derek. Normally getting slammed into walls wouldn't give him a boner, see entire High School Career of getting thrown into lockers without getting a hard on from it, but....

  
When they first started sleeping together it wasn't intentional and Derek had a minor breakdown about sleeping with a minor. The Alpha had been throwing Stiles around as per usual but, instead of following it up with a death threat he pushed the teenager down to his knees. The Spark had given blowjobs before, that much had been obvious, but Derek still felt awful about it..... It was literally a single week before Stiles turned eighteen. Eventually he got over it and stopped apologizing. 

  
The second time wasn't out of the adrenaline rush that manhandling gave Stiles, it was just before the Spark was going to turn nineteen and Derek booty called him. After that Stiles changed the Alpha's contact name to _Sexywolf_ and promptly annoyed the living hell out of the man until he fucked him just how he liked. 

They switched around alot, cue Stiles going almost hysterical from the wolf's reaction to him asking if they should keep record so they could take turns. 

  
It was a Monday, already certifiably the worst day of the week. Stiles had been sitting at his desk watching the clock and waiting on the edge of his seat for the final minute until the bell rang. When it did ring he went outside to the parking lot immediately, in no mood to deal with anyone. 

  
Derek was leaning against the side of his black Camero like some kind of model, his leather jacket and sunglasses accentuating all his assets. The glasses were resting on the top of his naturally ‘just got shagged’ black hair. He had a five o’clock stubble and a shirt tight enough to show his washboard abs. Stiles went directly to the Alpha, leaning next to him on the car. They made quite the picture together, two sexy adults with not a care in the world. 

  
“Can I interest you in a milkshake and curly fries before I take you back to mine?” Derek asked casually, like he wasn’t proposing sex in the middle of the school parking lot.

  
“Only if I can steal some of the strawberry shake you get and pretend to hate.” Stiles responded, already walking leisurely around the car to get into the passenger’s side. 

  
Derek just chuckled and got into the car, ignoring the admiring looks he inspired and drove them to the diner. The milkshakes were great and the conversation was even better, the Alpha would never admit it but he was a huge Marvel fan. 

As soon as they got back to the loft Derek pinned Stiles to the door, taking off their clothes as he walked them to the bed.

“Will you fuck me?” The wolf asked from where he was straddling the Spark’s thighs. 

Stiles just nodded and turned them over. He kissed Derek, the stubble leaving marks and only making him hotter. It was all tongue and teeth, lips bruised and puffy by the time they pulled away for air. Stiles kissed down Derek’s body, paying extra attention to the older man’s sensitive nipples and petting his happy trail. The Spark used a bit of his magic to let him leave marks without the wolf healing them, just laughing at the groan of pleasure and mock annoyance. 

Derek’s cock was completely hard and leaking by the time Stiles got down to it, his slow pace making the wolf growl at him when he completely avoided the hard on, instead only using one motion to pull back Derek’s thigh and lick a solid line right over his puckered hole.

When Derek was still panting at the sudden pleasure Stiles used the distraction to turn him onto all fours, burying his face back into the older man’s ass and rimming him for all he was worth. He circled the ring of tight muscles with the tip of his tongue until Derk started pushing back into it and begging for more, dipping in here and there to get the taste that was distinctly earthy and absolutely Derek. 

By the time Stiles had to pull back to get a full breath of air Derek was shaking in his desperation, handing him the lube, that he had time to get God only knows when, and thrusting his hips to get any sort of friction. 

Stiles just grabbed a firmer hold of the wolf’s shaking thighs and went back to sucking and biting at the rim, slicking his fingers and not giving any warning before adding one right alongside his tongue. Derek just moaned in need and pushed back into the penetrating finger. Stiles obliged the silent begging and added another finger instantly, pulling back to watch his fingers get swallowed by the tight heat of Derek’s body. 

“I’m ready, Stiles! Please!” The desperate Alpha begged when it became clear to his fogged mind that the Spark wasn’t going to move until he asked for it. 

Stiles just hummed, Derek’s clenching stomach only getting worse when he thought that Stiles wasn’t going to move before he swiftly removed his three fingers and slowly entered him before he had time to complain about the pace. Stiles never changed his speed, he never did. The Spark always started gentle, no matter the mood, then only changed the pace when Derek asked him to. It wasn’t anything other than a polite gesture that only made the wolf want the considerate boy more. 

Derek hung his head between his shoulder blades, his knees shaking and only staying up with the help of Stiles’ bracing hands. The wolf knew that he was allowed to take his time to get comfortable, one of his favorite things about Stiles, so he did. He waited until the cock inside him didn’t feel like a hot poker splitting him open and threatening to do it again, until he could shift and only feel pleasure with a hint of pain, not the other way around. 

The wolf nodded, groaning when Stiles instantly started thrusting. The movements were firm but still on the slower side until Derek tensed and practically screamed when he got a direct hit to the older man’s prostate. The wolf didn’t see the savage grin on Stiles’ face but it wouldn't have made a difference anyways.

Nothing could have prepared him for the harsh thrusts that lit up every nerve in his body. It was always amazing with Stiles, the sex different and unbelievably hot even when they went slow. Today wasn’t a slow day though. 

Stiles took his aggression out on the Alpha’s hole only sparing enough thought to make sure he hit the man’s prostate every time. He let the moans and keening cries of the man under him egg him on until he was going as hard and fast as he could, the hammering thrusts shaking the bed and getting grunts out of Derek every time. The man was shaking with the overwhelming pleasure, the never ending push and pull of the turgid flesh inside him never letting up and making him feel every inch. 

The teen’s moaning and sighs of pleasure made Derek fill with a different type of warmth, the kind he got when he made others happy. 

Derek came first, the constant pressure and occasional grinding alway hitting his prostate was too much. He could feel how swollen and sensitive his prostate was, the same way it usually was after a couple rounds with someone else, in just an hour. The wolf’s entire body clenched so tightly his rim burned against the cock that suddenly felt too big to take but he loved it, the pained edge only making his orgasm longer and helped along by Stiles never changing a thing about his thrusting. 

Stiles looked down, watching the way Derek’s tight hole tightened around him, practically swallowing his cock. The older man’s hole looked raw and was hotter than it was when they started, the abuse showing very visibly. The thought was what made Stiles finally come, curling over Derek’s back and growling in his ear as he released into the Alpha’s aching hole. 

After a while they finally got their bearings, Stiles getting up and coming back with a damp towel and water. He helped Derek with the water when it was clear he was still too shaky in the aftershocks as he cleaned them both up, being extra gentle at the man’s ruined hole and petting him when he whimpered at the empty, aching, pulsing his rim did. 

They laid around for a while, just stroking each other’s bodies and talking. There weren’t any expectations and it just made everything better. 

Stiles thought that if there was anyone in the world who understood him it was Derek.

They had other people they messed around with but they always came to each other when everything was simply too much. 

They didn't have a label for what they were, Stiles just said happy.

* * *

_I was having some formatting issues and Ao3 crashed for a while for me.... Rough day. Let me know if you have any pairings or prompts that you'd like to see from me. I had a lot going on recently but I promise I'll get to all of you eventually! -Rose_


End file.
